Tips For Nailing Your Next Executive Kickoff

By Chris Cancialosi

The launch of a new strategic effort represents a key opportunity for senior leaders to set things off on the right foot. Unfortunately, many senior executives fail to grasp the importance that a well prepared and delivered executive kickoff can have on the success of a project team.

This may happen because some leaders don’t take the time to develop the skills necessary to ensure that their kickoffs meet the mark or because they don’t see the inherent importance that their presence, statements, and interactions with others can have on their staff. Whatever the reason, or reasons, taking the time and effort to adequately prepare for this leadership responsibility can certainly pay dividends.

The start of a major, strategic effort within an organization usually represents the first official gathering of key stakeholders to formally organize and launch a process that holds the potential of having significant ramifications for your organization. These executives may serve as the champion of the initiative or, possibly, may simply be influential leaders who garner the respect and attention of people within the organization. In order to begin effectively, senior executives should begin by either setting the expectation for the new project or, should open and close the session with a few words of significance.

The executive kickoff components of these launches are meant to set a tone for the work effort, to clarify the vision, and to help the group understand the importance of what is being asked of them. Meetings such as these are also a time to clarify expectations, available support, as well as roles and responsibilities. They serve to frame the work and to form the team and they start the trust-building and relationship-building processes that can set the group up for success down the road. Finally, they serve as a ritual of sorts that signifies the start of something important.

Some senior executives have the rare ability to “wing it” during these kickoffs and to leave people informed, engaged, and inspired about the long road ahead without putting much preparation into the process. For the rest of us, success is contingent on some level of prior planning and the intentional development of skills to help us succeed in these situations.

We’ve seen instances in Canada where a canadian executive recruiter will easily spot executives who are trying to “wing it”, and will instantly be able to tell the “real deals” away from the “fakes”.

If you do not have a ton of experience planning for and conducting an executive kickoff, this may help you to organize your thoughts when you find yourself in such a position.

The initiative launch process.

The specific process by which organizations conduct project launch meetings can vary quite dramatically based upon factors such as the type of effort, the culture and various subcultures that exist within the organization, as well as the contextual variables in which the effort is being undertaken. Often, the executive kickoff portion of these meetings represents only a short portion of the typical process used to set the vision and expectations at the open or close of the meeting.

The launch meeting typically includes the following key elements:

Introductions: Taking a few minutes at the start of the meeting can help make people comfortable with each other, especially in large, complex organizations. One of the tangential benefits of bringing a diverse work team together is that they are afforded an opportunity to develop informal networks with people across the organization who they will now be partnering with to accomplish the task at hand. Don’t miss this chance to allow them to begin to develop these relationships.

The executive kickoff: This is your big chance (and just so it happens to be the focal point of this particular article). Once people are comfortable, you have a brief opportunity to set the stage and tone for the rest of the work that the team conducts. No pressure.

Vision for the work effort: Usually part of the executive kickoff, I call it out separately just to showcase the importance of this aspect of the meeting. People are looking to you to clearly articulate the purpose of the meeting and the work, to state your expectations, and to help them understand, right out of the gate, why this work is important to the success of your organization. While this and the remainder of the common components of the launch meeting are usually left for a program manager to handle, executives sometimes find themselves presenting this information in its entirety which is why I have included it here.

Discussion of roles, goals, and expectations: Providing team members an opportunity to clearly understand what role they will be playing in the effort and setting clear expectations can help to reduce or eliminate conflict moving forward.

Review of the project roadmap: This typically includes a high-level overview of the work plan, timelines, and key deliverables. This portion can look quite different from organization to organization based upon the level of maturity and the value your organization puts on formal project and program management practices.

Discussion around success criteria: Understanding what success looks like and helping team members to understand this helps to align around the target you are all trying to hit. How will you know that you have accomplished your task? What are the leading and lagging indicators that will let your team know that you are on the right track?

Assessment of risk: Engaging the group in dialogue on what risks exist that may hamper your efforts, what is the likelihood of them happening and what impact they may have can help the group begin to work toward mitigating or eliminating them through active management and attention. This is one component of launch meetings that can sometimes be missed.

Next steps: The table is now set and people will want to know what to do next. Be explicit about the next steps so that you don’t lose momentum before you’ve actually gotten out of first gear.

Close: In certain launch meetings, the close can serve as another opportunity for you, as the executive leader, to reinforce your key points. What are the 2-3 things that you want to make sure people walk away with?

Threats to success.

Regrettably, there are any number of factors that can put your kickoff at risk. These include, but are certainly not limited to:

Lack of preparation: There’s no excuse for not taking the time and effort to prepare. If you really hold the effort to be important enough to dedicate organizational resources to it, you owe the team your best self. Preparation may take different forms based on your level of experience delivering executive kickoffs but the only person you can blame for a failure of a kickoff is yourself if you don’t give it the attention it deserves.

Lack of authenticity: Trying to be something or someone you’re not rarely works. People see right through it and acting inauthentically will likely leave you feeling like a fraud. Understanding who you are as a leader as well as your unique strengths and weaknesses should help you guide your kickoff method so that it leverages your strengths and mitigates the risk associated with your weaknesses.

Lack of transparency: Nothing will kill people’s willingness to support your effort than coming off as if you are lying or withholding information from them. If you can’t honestly and openly discuss the details of the work effort, there are some red flags that should be addressed before bringing a team together to tackle it.

Forgetting why you’re doing this in the first place: While the executive kickoff presents an opportunity for you to assert and reinforce your beliefs, values, and expectations, remember that the real reason you are doing it is to ensure that your team gets started in the right direction. Don’t let it be all about you.

Getting off on tangents: If you are not crystal clear about the main points you are trying to convey during your kickoff, you run the real risk of getting off on tangents. This is especially true if you are uncomfortable speaking in front of groups.

Confirmation bias: Confirmation bias is a result of the human inclination to look for evidence that supports our beliefs and views while dismissing evidence contrary to our views. The threat here is that you begin to present your case using a false optimism that is only based on confirmatory data or evidence. The initiative can’t be important only because you think it’s important. What evidence is out there that supports or refutes your thinking?

Groupthink:Groupthink occurs when members of the group, in this case your kickoff team, value group harmony over the critical evaluation of objective data. Similar to confirmation bias, groupthink can threaten your kickoff if everyone in the meeting, for whatever reason, seeks to “go with the flow” rather than to question things when evidence to the contrary presents itself.

Tips for preparing an unforgettable executive kickoff.

Set the mood: You can take this concept as far as it suits your personal style but making an effort to set a mood can help to draw attention to your message. How is the room configured? Where will you sit or stand? What technology might you utilize (or not) to help you convey your message? The nonverbal aspects of your kickoff will undoubtedly send messages to your audience and shouldn’t be overlooked.

Work with the project team leadership to understand how you can best set them up for success: In many cases, your executive kickoff will serve as a table setting for a longer meeting run by a project lead or program manager. Working with this team to understand how your kickoff can best support their objectives and what your keys messages should be can be extremely helpful in ensuring alignment and in helping to set them up for success.

Get everyone together physically if possible but make sure everyone is there. Although this is not always possible logistically, attempting to bring the team together, in person, for the kickoff can have many positive effects. If this isn’t an option for whatever reason, ensuring that everyone attends via video conference can be an adequate next best alternative. This is your chance to align everyone so having everyone involved in the process is really important.

Make sure everyone is involved in the process: If your role is solely to kick the meeting off, this item may be more important for your project lead or program manager to consider when preparing for the kickoff meeting. Finding ways to minimize the ‘talking head’ aspects of the meeting and ensuring that there are opportunities throughout the process to actively engage participants in contributing input and ideas to the process will not only help keep people’s attention but it can dramatically increase the amount of ownership and buy-in they have to the process.

Keep it short! No matter how interesting and charismatic you are (or think you are), droning on and on will lose people and distract from what you are really there for. Keep your points brief and stay on task. If you are handing the meeting off to a project lead or program manager, be sure that you set them up for success.

Keep it casual: Casual can be defined in many ways based on the culture of your organization but unless your goal is to set a tone that is extremely formal and rigid, try to loosen it up a bit. Make it personal and appeal to both the minds and the hearts of your audience.

Tie it to the strategy/bigger picture: Explicitly tying the work effort to the bigger picture of success of your organization will appeal to people’s minds. Facts and data and a clear link between this work that you are about to embark on and your team’s collective success will help people understand why it’s so important.

Tell a story/make it personal: Appealing to people on a personal level is just as important. Personalizing your kickoff by telling a short anecdote can help you make your key points in a way that balances the conversation with something that hits people in their hearts. Exposing your true self and a bit of your own story can help to establish a sense of openness and vulnerability right from the start.

Make it fun: Again, “fun” can take on many meanings depending on the culture of your organization but a kickoff of an important initiative is a time to generate some excitement. Make people feel special and help them understand why they are in the room.

Provide space for people to get to know each other: This can be especially important in large organizations where people may be meeting and working with each other for the first time. Creating space for team members to get to know each other, to expand their informal networks, and to begin to develop trusting relationships with each other can be critical to your long-term success.

Review documentation prior to the meeting: Bringing people together to meet is a very expensive endeavor. Where appropriate, try to provide information to team members to review prior to attending the kickoff so that you can utilize the limited time together to do things that are more conducive to discussing live as a group.

Think about what questions people may have and proactively address them: Understanding your stakeholders and working to identify and proactively address questions and concerns that they may likely have during the kickoff can significantly reduce the amount of time spent reacting to questions and concerns in the meeting itself.

Rehearse, rehearse, rehearse (and solicit feedback): As the saying goes, “perfect practice makes perfect”. Setting aside time to rehearse your messaging can pay off in spades. Soliciting feedback from others can help you sharpen your points and can help you feel more comfortable delivering your message to others.

Final thoughts.

Making the time to capitalize on the opportunity to plan and deliver a clean, clear, and inspirational executive kickoff can not only give your team a leg up as they embark on your next strategic initiative but it can serve as an opportunity for you to reinforce your presence as a leader. To reiterate what’s most important to you and to the organization and to show confidence in your team don’t miss these chances by underpreparing or skipping them altogether. Failing in these moments sends powerful messages to your team as well. Unfortunately, they are not the messages you are likely intending to convey. If you think you can convey those powerful messages to your team and you’re looking for interim executive jobs, my friend recommended Suzie Walker Executive Search. They offer a bespoke service to find the top talent to lead your business/organisation.

Chris Cancialosi is a recognized expert in the field of leadership and organizational development with particular focus on the leader’s role in shaping high-performing culture. Chris effectively combines his operational field experience with his knowledge of organizational psychology to provide unique and practical solutions to today’s ever changing business landscape.